16312-21-3

Basic information

• Product Name: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE
• Synonyms: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE
• CAS NO: 16312-21-3
• Molecular Formula: C₄H₅NO₂S
• Molecular Weight: 131.15
• Mol File: 16312-21-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 40-43°C
• Boiling Point: 204.7°Cat760mmHg
• Flash Point: 77.6°C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 0.26mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.27±0.20(Predicted)
• CAS DataBase Reference: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE(16312-21-3)
• EPA Substance Registry System: 3-METHYL-1,3-THIAZOLANE-2,4-DIONE(16312-21-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16312-21-3(Hazardous Substances Data)

Usage

Description

3-METHYL-1,3-THIAZOLANE-2,4-DIONE is an organic compound that serves as a versatile intermediate in both organic synthesis and pharmaceutical applications. It is characterized by its unique chemical structure, which includes a thiazolidine ring and a dione functional group. 3-METHYL-1,3-THIAZOLANE-2,4-DIONE is primarily utilized in laboratory research and development processes, as well as in chemical production.

Uses

Used in Organic Synthesis:
3-METHYL-1,3-THIAZOLANE-2,4-DIONE is used as an organic synthesis intermediate for the production of various chemical compounds. Its unique structure allows it to be a key component in the synthesis of a wide range of organic molecules, making it valuable in the development of new materials and chemical products.
Used in Pharmaceutical Industry:
3-METHYL-1,3-THIAZOLANE-2,4-DIONE is used as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and pharmaceuticals. Its presence in the synthesis process can contribute to the creation of novel therapeutic agents, potentially leading to advancements in medicine and healthcare.
Used in Laboratory Research and Development:
3-METHYL-1,3-THIAZOLANE-2,4-DIONE is employed in laboratory research and development processes, where it is used to explore its potential applications and properties. This can lead to a better understanding of the compound and its possible uses in various industries, including the development of new chemical processes and products.
Used in Chemical Production Process:
3-METHYL-1,3-THIAZOLANE-2,4-DIONE is utilized in the chemical production process, where it contributes to the manufacturing of various chemical products. Its presence in the production process can enhance the efficiency and effectiveness of the overall chemical synthesis, leading to improved product quality and performance.

Synthesis

To a solution of 2,4-thiazolidinedione (1 equiv) in 5 mL of DMF was added potassium carbonate (1.1 equiv) and halogen (1.1 equiv). The suspension was stirred at 80 oC overnight. Solvent was evaporated and the residue was purified by flash column chromatography ( petroleum ether/EtOAc, 5:1) to afford the product 3. 3-Methylthiazolidine-2,4-dione (3a) Following the previous procedure, 2,4-thiazolidinedione (500 mg, 4.3 mmol) and iodomethane (0.3 mL, 4.7 mmol). 3a as white solid (460 mg, 82%).

InChI:InChI=1/C4H5NO2S/c1-5-3(6)2-8-4(5)7/h2H2,1H3

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 19708-85-1 methyl-thiocarbamic acid O-cyclohexyl ester 
• 79-08-3 bromoacetic acid 
• 71-43-2 benzene 
• 114710-77-9 3-Methyl-2-[(Z)-pyridin-2-ylimino]-thiazolidin-4-one 
• 65645-28-5 methyl-thiocarbamic acid O-menthyl ester 
• 77-78-1 dimethyl sulfate 
• 39131-10-7 1,3-thiazolidine-2,4-dione potassium salt 
• 1239279-47-0 C₁₆H₁₄BrN₃O₄S₂ 
• 1239279-42-5 C₁₆H₁₄BrN₃O₅S 
• 598-21-0 2-Bromoacetyl bromide 
• 598-52-7 1-(methyl)-thiourea 

Downstream Products

• 2365-48-2 Methyl thioglycolate 
• 68-11-1 mercaptoacetic acid 
• 74-89-5 methylamine 

Relevant articles and documents

Design, synthesis,: In silico molecular modelling studies and biological evaluation of novel indole-thiazolidinedione hybrid analogues as potential pancreatic lipase inhibitors

Pancreatic lipase (PL) is a key enzyme responsible for the digestion of dietary triglycerides; hence its inhibition is considered as a promising target for the management and/or treatment of obesity. A new series of indole-thiazolidinedione (TZD) hybrid analogues were synthesized using a molecular hybridisation approach and evaluated for their anti-obesity effects via PL inhibition. The targeted analogues were synthesized via the condensation reaction between various substituted isatin with TZD in the presence of aqueous KOH in methanol. Amongst the synthesized analogues, 7k and 7m exhibited a potential PL inhibitory activity (IC50-7.30 and 9.51 μM, respectively). Kinetic study of these potent analogues revealed their competitive mode of enzyme inhibition. This fact was confirmed via fluorescence spectroscopy which further suggested the presence of one binding site for the synthesized analogues. Molecular docking of the synthesized analogues was performed using human PL (PDB ID: 1LPB). The obtained MolDock scores were aligned with the in vitro PL inhibitory activity (Pearson's r = 0.9108, p 0.05). Moreover, a stable conformation of the 1LPB-ligands suggested the stability of these complexes in the dynamic environment. These studies provided a basis for the potential role of the indole-TZD hybrids in PL inhibition and further optimization might result in the development of new lead candidates for obesity treatment.

Design, synthesis and biological evaluation of novel 6-phenyl-1,3a,4,10b-tetrahydro-2H-benzo[c]thiazolo[4,5-e]azepin-2-one derivatives as potential BRD4 inhibitors

Bromodomain-containing protein 4 (BRD4) is a key epigenetic regulator in cancer, and inhibitors targeting BRD4 exhibit great anticancer activity. By replacing the methyltriazole ring of the BRD4 inhibitor I-BET-762 with an N-methylthiazolidone heterocyclic ring, fifteen novel BRD4 inhibitors were designed and synthesized. Compound 13f had a hydrophobic acetylcyclopentanyl side chain, showing the most potent BRD4 inhibitory activity in the BRD4-BD1 inhibition assay (IC50 value of 110 nM), it also significantly suppressed the proliferation of MV-4-11 cells with high BRD4 level (IC50 value of 0.42 μM). Furthermore, the potent apoptosis-promoting and G0/G1 cycle-arresting activity of compound 13f were indicated by flow cytometry. As the downstream-protein of BRD4, c-Myc was in significantly low expression by compound 13f treatment in a dose-dependent manner. All the findings supported that this novel compound 13f provided a perspective for developing effective BRD4 inhibitors.

cGAS ANTAGONIST COMPOUNDS

Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.